(2-ethenylphenyl)boronic acid

Conditions: temp:0.00; pressure:0.00; stir:

Conditions: temp:0.00; pressure:0.00; stir:

Conditions: temp:0.00; pressure:0.00; stir:

Conditions: temp:0.00; pressure:0.00; stir:

Conditions: temp:0.00; pressure:0.00; stir:

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: Methyl 5-bromo-6-cyclohexyl-4H-thieno[3,2-b]pyrrole-2-carboxylate (prepared as described in Example 7, Step 1) and (2-vinylphenyl)boronic acid (1.5 eq.) were dissolved in dioxane (0.06 M) and 2M aq. Na2CO3 (6 eq.) was added. The solution was degassed by bubbling argon, Pd(PPh3)2Cl2 (0.2 eq.) was added, and the reaction mixture was placed in an oil bath preheated to 110° C. and stirred for 1 h; after removing all volatiles the title compound was isolated by chromatography (PE/EtOAc 10:1). Yield: 71%. 1H-NMR (400 MHz, CDCl3, 300 K, δ) 8.16 (bs, 1H), 7.69 (d, 1H, J 7.9), 7.68 (s, 1H), 7.45-7.35 (m, 3H), 6.67 (dd, 1H, J 17.5, 11.0), 5.74 (d, 1H, J 17.5), 5.25 (d, 1H, J 11.0), 3.91 (s, 3H), 2.54-2.47 (m, 1H), 1.81-1.23 (m, 10H); MS (ES+) m/z 366 (M+H)+. The solution was degassed was added the reaction mixture was placed in an oil bath preheated to 110° C. after removing all volatiles the title compound was isolated by chromatography (PE/EtOAc 10:1)

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: Following the procedure outlined for Examples 41–107, reaction of 2-vinyl-phenylboronic acid (30 mg, 0.20 mmol, Aldrich Chemical Company), {[4-(3-bromo-benzenesulfonyl)-5-methylsulfanyl-thiophen-2-yl]-imino-methyl}-carbamic acid tert-butyl ester (50 mg, 0.1 mmol, as prepared in Example 27, step c), tetrakis(triphenylphosphine)palladium(0) (29 mg, 0.025 mmol, Strem Chemicals, Inc., Newburyport, Mass.), Na2CO3 (400 μL, 2M aqueous), and toluene/EtOH mixture (2:1, 1.2 mL) afforded 25 mg (50%) after purification (1:3 EtOAc/hexanes, 2000μ SiO2 plate) of the title compound as a white foam. afforded 25 mg (50%) after purification (1:3 EtOAc/hexanes, 2000μ SiO2 plate) of the title compound as a white foam

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: Following the procedure outlined for Examples 41–107, reaction of 2-vinyl-phenylboronic acid (30 mg, 0.20 mmol, Aldrich Chemical Company), {[4-(3-bromo-benzenesulfonyl)-5-methylsulfanyl-thiophen-2-yl]-imino-methyl}-carbamic acid tert-butyl ester (50 mg, 0.1 mmol, as prepared in Example 27, step c), tetrakis(triphenylphosphine)palladium(0) (29 mg, 0.025 mmol, Strem Chemicals, Inc., Newburyport, Mass.), Na2CO3 (400 μL, 2M aqueous), and toluene/EtOH mixture (2:1, 1.2 mL) afforded 25 mg (50%) after purification (1:3 EtOAc/hexanes, 2000μ SiO2 plate) of the title compound as a white foam. afforded 25 mg (50%) after purification (1:3 EtOAc/hexanes, 2000μ SiO2 plate) of the title compound as a white foam

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: The reaction was performed with 2-vinyl-phenylboronic acid (10 g, 0.0676 mol), 2-bromopyridine (12.64 g, 0.08 mol), tetrahydrofuran (100 ml), 2M potassium carbonate aqueous solution (26 ml), and tetrakis(triphenylphosphine) palladium (Pd(Ph3)4, 0.06 g, 1 mol %) according to Example 1. The yield was 75%.

Conditions: temp:0.00; pressure:0.00; stir:

Conditions: temp:0.00; pressure:0.00; stir:

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: Add 0.5 ml of 2 M aqueous potassium carbonate solution to a mixture of 224 mg (0.50 mmol) 6-{[6-bromo-5-(4-methoxyphenyl)furo[2,3-d]pyrimidin-4-yl]amino}hexanoic acid methyl ester and 29 mg (0.03 mmol) tetrakis(triphenylphosphine)palladium(0) in 2.5 ml 1,2-dimethoxyethane. Next, add 92 mg (0.63 mmol) (2-vinylphenyl)boronic acid and stir the mixture for 15 h under reflux. Filter the reaction mixture and purify directly by preparative RP-HPLC (gradient: water/acetonitrile). 82 mg (35% of theor.) of the desired product is obtained. under reflux Filter the reaction mixture purify directly by preparative RP-HPLC (gradient: water/acetonitrile)